In a medium mixing bowl, whisk together the instant vanilla pudding mix and whole milk until smooth and thickened, about 2 minutes.
Add the creamy peanut butter to the pudding mixture and whisk until fully combined and smooth.
In a separate chilled mixing bowl, beat the heavy whipping cream, granulated sugar, and vanilla extract with an electric mixer until stiff peaks form.
Gently fold half of the whipped cream into the peanut butter pudding mixture until well combined.
In a large clear trifle bowl or individual serving glasses, start layering: place one-third of the broken peanut butter cookies at the bottom.
Spoon one-third of the peanut butter pudding mixture over the cookies, spreading evenly.
Sprinkle one-third of the chopped roasted peanuts over the pudding layer.
Repeat the layering process two more times, ending with a layer of whipped cream on top.
Finish by sprinkling the remaining chopped peanuts on the top whipped cream layer.
Refrigerate the trifle for at least 2 hours before serving to allow flavors to meld and layers to set.